Ethoxyethylamine → HCID 86612785, compound

HRID 2364442Notes

Reaction equation

HRID 2364442 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:39])=[C:14]([C:34](OCC)=[O:35])[C:15](=[O:33])[N:16]3[CH2:19][CH2:20][N:21]([CH3:32])[C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.C([O:42][CH2:43][CH2:44][NH2:45])C>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:39])=[C:14]([C:34]([NH:45][CH2:44][CH2:43][OH:42])=[O:35])[C:15](=[O:33])[N:16]3[CH2:19][CH2:20][N:21]([CH3:32])[C:22](=[O:23])[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:11][CH:10]=2)=[CH:6][CH:7]=1.[NH2:11][CH2:12][CH2:13][OH:39]

Participants

4

Reactant 2

HCID 66970EthoxyethylamineHCID 69482645HCID 69482645, compound

Product 1

HCID 86612785HCID 86612785, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate(0.022 g, 0.041 mmol) in EtOH (3 mL) under nitrogen was treated with Ethoxyethylamine (0.012 mL, 0.20 mmol) for 15 min.@150° C. in a microwave vessel then@150° C. for an additional 1 h. After the reaction was cooled to ambient temperature the resulting suspension was filtered, and the filtered solid was washed with EtOH and Et2O then thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6 (90° C.) δ ppm 2.62 (t, J=5.67 Hz, 2 H), 2.87 (s, 3 H), 3.38 (t, J=7.14 Hz, 2 H), 3.43-3.49 (m, 2 H), 3.55 (t, J=5.95 Hz, 2 H), 3.60 (s, 3 H), 4.07-4.15 (m, 3 H), 4.41 (t, J=5.67 Hz, 3 H), 4.64 (s, 1 H), 4.87 (s, 2 H), 7.08 (t, J=8.97 Hz, 2 H), 7.16 (s, 2 H), 7.28 (d, J=2.20 Hz, 2 H), 7.29-7.34 (m, 3 H), 7.87 (s, 1 H), 8.48 (s, 1 H), 10.30 (s, 1 H); ES+ MS: 549 (M+H+).

Workup

  1. filtrationwas filtered
  2. washthe filtered solid was washed with EtOH and Et2O
  3. customthen thoroughly dried under high vacuum

Sources & evidence

ORD record
ord-5b30a18b7fab495e8458d2b8353ce235
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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